The tie off sides are clearly delineated with writing next to the string holes. Maybe I'm not thinking about this correctly, but it seems like if you don't start your initial crosses in the right spot, you could potentially tie off on the opposite side of the racket which may or may not even be an issue.

Nope. For you to "start in the wrong spot", you would have to be off one hole... which would mean the string would pull right through the O-ports. The O-ports design makes it impossible to be off one hole. So no need to worry, if your crosses are in, it will always lead to the right tie off.